Aminosugars. XXII. Syntheses and Properties of 6-Deoxy-6-and 3-Deoxy-3-guanidino-D-hexoses

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概要

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• Methyl 6-deoxy-6-guanidino-α-D-glucopyranoside, 6-deoxy-6-guanidino-D-galactose, 3-deoxy-3-guanidino-D-allose (<B>7</B>), and 3-deoxy-3-guanidino-D-glucose were synthesized by guanidination of the corresponding amino-sugars. The acetate of <B>7</B> was proved to exist in a bicyclic structure; 2′,4′,6′-tri-<I>O</I>-acetyl-D-allopyrano[l′,2′,3′;4,5,6]-2-acetylimino-1,3-diacetyl-perhydropyrimidine, whereas others exist as the usual pyranoses. Properties of the new compounds and the synthetic methods were examined.

• 公益社団法人 日本化学会の論文

著者

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Sekiya Tetsuo

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Ogura Yoshio

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

関連論文

• Branched-chain Sugars. XVII. Stereoselectivity in the Oxidation of Several Methyl 4,6-O-Benzylidene-2-C- or -3-C-methylene-α- and-β-D-hexopyranosides with m-Chloroperbenzoic Acid
• Branched-Chain Sugars. I. On the Configuration of Branched-Chain Derivatives of 1,2 : 5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose
• Branched-chain Sugars. VIII. On the Configuration of Branched-chain Sugars from Methyl 3-O-Benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose
• Studien über D-Glucosamin-derivaten. VII. Darstellung von 3, 4; 5, 6-Di-O-isopropyliden-N-acetyl-D-glucosaminsäure über das entsprechende D-Glucosaminol-derivat
• Branched-chain Sugars. VI. Reaction of Methylene Dimagnesium Bromide with Uloses
• Aminosugars. XXVIII. A Facile Synthesis of Benzyl α- and β-Kasugaminides via the Corresponding Abequosides
• Branched-chain Sugars. XXXV. The Synthesis of L-Rubranitrose (2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-xylo-hexopyranose)
• Synthesis of 4-(D-alanylamino)-2-amino-2,4-dideoxy-D-xylose.
• The synthesis and reaction of spiro(oxolane-2,2'-piperazine)-3',6'-diones with N-bromosuccinimide in the presence or absence of water.
• Branched-chain sugars. XXII. Synthesis of benzyl 2,3-di-O-benzyl- and 2,3-O-methylene-.BETA.-L-threo-pentopyranosid-4-uloses, and the corresponding 6-deoxy-.ALPHA.-D-xylo-hexopyranosid-4-uloses.
• .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIII. The synthesis and configuration of alkyl 2-acylamino-2-alkenoates and their cyclized 2,5-piperazinedione derivatives.
• Branched-chain sugars. XXVIII. Synthesis of 2-C-methyl-L-glyceraldehyde, 2-C-methyl-D-erythrose, and 3-C-methyl-L-erythrose derivatives.
• Quantitative Estimation of the Fehling Reaction of 1-O-Protected Uronic Acids
• Syntheses of N-Substituted Carbamimidoylformic Acids
• Aminosugars. XXVI. Synthesis of amido-bonded disaccharides containing hexosaminuronic acids.
• Dehydrooligopeptides. III. Synthesis of (Z,Z)- and (Z,E)-geometric isomers of dehydrodipeptides and their base-catalyzed transformation to the hydantoin derivatives.
• The confirmation of the configuration of ethyl 2-bromo-3-nitro-2-alkenoate by 13C NMR spectroscopy.
• Asymmetric Reactions. VI. Asymmetric Hydrogenation of Atropate Catalyzed by Cyanocobalt-Opticall Active Diamine Complex
• Asymmetric Reactions. V. Homogeneous Hydrogenation of Unsaturated Compounds Catalyzed by Bis(dimethylglyoximato)cobalt(II)
• Preparations and properties of optically active (alkyl)bis(dimethylglyoximato)cobalt(III) complexes.
• Asymmetric Hydrogenation Catalyzed by Bis(dimethylglyoximato)cobalt(II)-Optically Active Amine Complex
• .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XVII. The facile synthesis of ethyl .ALPHA.-azido-.ALPHA.-alkenoates and reduction to ethyl .ALPHA.-amino-.ALPHA.-alkenoates.
• .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIV. The synthesis and reduction of Diels-Alder adducts from ethyl 3-nitro-2-alkenoates and cyclopentadiene.
• .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XV. The reaction of ethyl 3-nitro-2-alkenoate with bromine azide or bromine, and transformations of the products.
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• Dehydrooligopeptides. II. The synthesis of dehydrodehydrodipeptides by direct coupling and base-catalyzed .BETA.-elimination.
• A Novel Synthesis of Ethyl β-Diethoxyphosphinyl-α,β-unsaturated-carboxylates
• The formation of the main skelton of bicyclomycin by the cyclization of 6-hydroxy-3-(3-hydroxypropyl)-2,5-piperazinedione derivatives.
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• .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIX. The convenient synthesis of .ALPHA.-alkoxy-, .ALPHA.-hydroxy-.ALPHA.-amino acid, and its cyclic dipeptide from .ALPHA.-dehydroamino acid.
• A convenient synthesis of 6-hydroxy-7,9-bis(p-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo(4.2.2)decane-8,10-dione.
• Aminosugars. XXXI. Preparation of benzyl 2-acylamino-4-azido-2,4-dideoxy-ribo- and -lyxopyranosides by inversion of hydroxyl group on C-3.
• Aminosugars. XXIII. L-Idofuranose Derivatives Containing a Heterocycle at C-5,6 Position
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• Amino sugars. XXXII. Ammonolysis and azidolysis of benzyl 2,3-anhydro-4-azido-4-deoxypentopyranosides.
• Branched-chain Sugars. III. Addition of Vinylmagnesium Bromide to 5,6-Dideoxy-1,2-O-isopropylidene-6-C-nitro-3-O-substituted-α-D-xylo-hex-5-enof uranoses
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• Branched-chain Sugars. IV. Synthesis of 5,6-Dideoxy-5-C-hydroxymethyl-1,2-O-isopropylidene-6-C-nitro-3-O-substituted-α-D-glucose Derivatives
• The Reaction of β-Nitroalcohols and Reactive Aldehydes
• An Attempted Synthesis of 3,6-Epidithio-2,5-piperazinedione by Cyclization of N,N′-dialkyl-2,2′-dithiodicinnamamide
• α,β-Unsaturated Carboxylic Acid Derivatives. VIII. The Synthesis and Reaction of Esters N-Acyl-N-bromo-α-dehydroamino Acid
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• .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XVI. Synthesis and configuration of Diels-Alder adducts from ethyl 3-nitro-2-alkenoate and 1,3-butadiene.
• Asymmetric reactions. X. Asymmetric hydrogenation catalyzed by bis(dimethylglyoximato)cobalt(II)-chiral cocatalyst (amino alcohol) system.
• α,β-Unsaturated Carboxylic Acid Derivatives. VI. New Synthesis of N-Acyl-α-dehydroamino Acid Esters
• α,β-Unsaturated Carboxylic Acid Derivatives. X. The Synthesis and Reaction of α-Azido-diethoxyphosphinyl-α- and β-alkenes
• Studies on Nitro Carboxylic Acids. III. The Reaction of α-Nitroolefins with Triethyl or Diethyl Phosphite
• Branched-chain sugars. XXXIV. Synthesis of methyl dihydroeurekanate.
• .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XI. Convenient synthesis of tert-butyl 2-alkoxy- and hydroxy-2-acetylamino-3-mono- or 3,3-dihaloalkanoates.
• Asymmetric Reactions. IV. An Attempted Asymmetric Reduction by a Solution of [Co(CN)5]3− and Optically Active α-Amino Acid, and Its Reactive Species
• A facile synthesis of 3-(1-benzyloxymethyl-3-hydroxypropyl)-2,5-piperazinedione.
• Synthetic studies on glycocinnamoylspermidine. II Synthesis of 4-O-(2-azido-2-deoxy-D-xylopyranosyl)-2-azido-2-deoxy-D-xylopyranose derivatives.
• Branched-chain sugars. XI. Synthesis of 2,3,6-trideoxy-3-C,4-O-dimethyl-3-nitro-D-arabino-hexopyranose (D-Evernitrose).

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